3-[(Methyl­carbamo­yl)amino]-1H-isoindolium chloride

Bushra Maliha; Muhammad Ilyas Tariq; M Nawaz Tahir; Ishtiaq Hussain; Hamid Latif Siddiqui

doi:10.1107/S1600536809003699

. 2009 Feb 4;65(Pt 3):o448. doi: 10.1107/S1600536809003699

3-[(Methylcarbamoyl)amino]-1H-isoindolium chloride

Bushra Maliha ^a, Muhammad Ilyas Tariq ^b, M Nawaz Tahir ^c,^*, Ishtiaq Hussain ^d, Hamid Latif Siddiqui ^a

PMCID: PMC2968434 PMID: 21582121

Abstract

The title compound, C₁₀H₁₂N₃O⁺·Cl⁻, is a derivative of o-phthaldehyde and methylthiourea. The molecules form dimers through intra- and intermolecular N—H⋯O hydrogen bonds. The dimers are further linked into chains through one C—H⋯Cl and two N—H⋯Cl hydrogen bonds.

Related literature

For applications of iminium salts, see: Page et al. (2008 ▶); Skalkos et al. (1994 ▶) Tariq et al. (2008 ▶). For the formation of derivatives of o-phthaldehyde with different ureas, see: Maliha, Tariq, Tahir, Hussain & Ali (2009 ▶); Maliha, Tariq, Tahir, Hussain & Siddiqui (2009 ▶); Maliha et al. (2008 ▶). For a related structure, see: Arfan et al. (2008 ▶).

Experimental

Crystal data

C₁₀H₁₂N₃O⁺·Cl⁻
M _r = 225.68
Triclinic,
a = 7.1171 (5) Å
b = 7.7900 (6) Å
c = 10.3033 (8) Å
α = 89.484 (3)°
β = 69.997 (2)°
γ = 74.613 (4)°
V = 515.43 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 296 (2) K
0.30 × 0.10 × 0.06 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.982, T _max = 0.989
8853 measured reflections
2369 independent reflections
2210 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.101
S = 1.01
2369 reflections
146 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.69 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809003699/ez2156sup1.cif

e-65-0o448-sup1.cif^{(19KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809003699/ez2156Isup2.hkl

e-65-0o448-Isup2.hkl^{(114KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1	0.81 (2)	2.22 (2)	2.7097 (16)	119.9 (18)
N1—H1N⋯O1ⁱ	0.81 (2)	2.15 (2)	2.8760 (17)	150 (2)
N2—H2N⋯Cl1ⁱⁱ	0.90 (2)	2.23 (2)	3.0969 (13)	160.5 (18)
N3—H3N⋯Cl1ⁱⁱ	0.86 (2)	2.40 (2)	3.2082 (13)	157.0 (17)
C1—H1B⋯Cl1ⁱⁱⁱ	0.97	2.74	3.6755 (16)	162

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

The authors acknowledge the Higher Education Commission, Islamabad, and the University of the Punjab, Lahore, Pakistan, for funding the research.

supplementary crystallographic information

Comment

Iminium salts are a class of organic compounds acting as reactive intermediates. These are being extensively synthesized and further reacted in an efficient and convenient manner for the preparation of multidrug-resistance reversal agents and pesticides and for metal complexation to form new photosensitizers (Page et al., 2008; Skalkos et al., 1994; Tariq et al., 2008). The present paper relates to the continuation of our studies regarding the formation of derivatives of O-phthaldehyde with different ureas (Maliha et al., 2008; Maliha, Tariq, Tahir, Hussain & Ali, 2009; Maliha, Tariq, Tahir, Hussain & Siddiqui, 2009).

The molecule of the title compound (I; Fig 1), is almost planar. It has three N—H bonds in the asymmetric unit. The N—H of the pyrrole ring forms an intramolecular as well as an intermolecular N–H···O H-bond. The title compound forms a dimer (Fig 2) with a central four membered O···H···O···H unit. The other two N–H groups in the methyl urea moiety are involved in intermolecular H-bonding with the Cl^-. The Cl^- also forms H-bonds with the methylene group of the pyrrole ring. Consequently, the chlorine anion makes three H-bonds. Similar Cl^- bonding behavior has been reported by Arfan et al. (2008). No strong π interactions are observed.

Experimental

O-phthaldehyde (200 mmol), methylthiourea (200 mmol) and a few drops of 2M HCl were mixed and ground in mortar and pestle. The product obtained was washed sequentially with hexane, ether, ethanol and water. The precipitate was dried and recrystallized from a mixture of methanol:acetone (9:1), by slow evaporation at room temperature.